Esters of fatty acids and juvenoid alcohols, and a method of their preparation and use

ABSTRACT

Esters derived from fatty acids and juvenoid alcohols of the general formula (I), in which X means the oxygen atom or the NH group, Y means the NH group or the oxygen atom, R means methyl, ethyl, 1-propyl, 2-methylethyl or propargyl and R′ means saturated or unsaturated alkyl with 4 to 22 carbon atoms. Esters derived from fatty acids and juvenoid alcohols are produced by a reaction of a juvenoid alcohol of the general formula (II), in which X means the oxygen atom or the NH group, Y means the NH group or the oxygen atom and R means methyl, ethyl, 1-propyl, 2-methylethyl or propargy] with a fatty acid chloride of the general formula (III): R′COC1 in which R′ means saturated or unsaturated alkyl with 4 to 22 carbon atoms, under the continuous stirring, at 0 to 70° C., using a convenient solvent, as toluene, xylene or benzene and under the presence of a base catalyst, as triethylamine, pyridine or quinoline. The compounds claimed in the claim 1 of the general formula (I) are applied for the insect population density control.

TECHNICAL FIELD

The invention relates to esters derived from fatty acids and juvenoidalcohols, a method of their preparation and use for reduction of insectpopulation density.

BACKGROUND ART

The studies of juvenoids, compounds imitating the effect of naturalinsect juvenile hormone on insect development and reproduction, haverepresented an intensively studied field since mid-sixties of thiscentury. A number of monographies and reviews (e.g. Sláma K., Roma{haeckover (n)}uk M, {haeck over (S)}orm F.: Insect Hormones and Bioanalogues,Springer, 1974; Henrick C. A.: Juvenoids; in the book Agrochemicals fromNatural Products (C. R. A. Godfrey, ed.), pp. 147-213 (1995); Wimmer Z.,Rejzek M., Zarevúcka M., Kuldová J., Hrdý I., N{haeck over (e)}mec V.,Roma{haeck over (m)}uk M.: J. Chem. Ecol. 23, 605-628 (1997)) supportthis statement. Recently, the attention has also been focused on amodified type of the compounds, which display the effect on insectdevelopment and reproduction, on juvenogens (Sláma K., Roma{haeck over(n)}uk M.: Insect Biochem. 6, 579-586 (1976); Wimmer Z., Rejzek M.,Zarevúcka M., Kuldová J., Hrdý I., N{haeck over (e)}mec V., Roma{haeckover (n)}uk M.: J. Chem. Ecol. 23, 605-628 (1997)). During designing anddeveloping of these new compounds, selected ways of transformation ofcertain functionalities in the juvenoid molecules have been applied,resulting in a formation of a new functionality, e.g. esterfunctionality, replacing of the original functionality, e.g. alcoholicfunctionality, through which transformation physico-chemical propertiesof the new compound are different from the physico-chemical propertiesof the original compound. Changes in the physico-chemical properties ofthe compounds are connected with possible changes of practicalapplication of the new compound as well.

DISCLOSURE OF INVENTION

1. The subjects of this invention are esters derived from fatty acidsand juvenoid alcohols of the general formula I,

in which X is oxygen or the NH group,

Y is the NH group or oxygen,

R is methyl, ethyl, 1-propyl, 2-methylethyl or propargyl and

R′ is a saturated or an unsaturated alkyl with 4 to 22 carbon atoms.

2. The esters derived from fatty acids and juvenoid alcohols claimed inthe claim 1 are prepared using a method that the juvenoid alcohol of thegeneral formula II,

in which X is the oxygen atom or the NH group,

Y is the NH group or the oxygen atom,

R is methyl, ethyl, 1-propyl, 2-methylethyl or propargyl is allowed toreact with the chloride of a fatty acid of the general formula III,

R′COCl  (III)

in which R′ is a saturated or an unsaturated allyl with 4 to 22 carbonatoms, under the continuous stirring, at 0 to 70° C., using a convenientsolvent, as toluene, xylene or benzene and under the presence of a basecatalyst, as triethylamine, pyridine or quinoline.

3. The esters derived from fatty acids and juvenoid alcohols claimed inclaim 1 are used for the insect population density control, with specialfocus on the control of insects of the orders Isoptera, Blattodea,Diptera, Hymenoptera, Orthoptera, Coleoptera, and Lepidoptera. Theesters derived from fatty acids and juvenoid alcohols claimed in theclaim 1 display different chemical structure compared with the chemicalstructure of the original juvenoids and display also differentphysico-chemical properties compared with the properties of the originaljuvenoids, especially their melting points, through which they displaydifferent volatility and polarity, and these differences enabledifferent way of practical application of the compounds claimed in theclaim 1 against target insect species, and the esters derived from fattyacids and juvenoid alcohols claimed in claim 1 display higher stabilityin comparison with the stability of the original juvenoids and areresponsible for improved dosage of the compounds claimed in the claim 1during the screening against insect species. The compounds claimed inthe claim 1 also enable a more effective way of practical applicationand due to their improved physico-chemical properties they also displaya longer effect under the field conditions. The compounds claimed in theclaim 1 are environmentally safe compounds, which are metabolized in away through which no toxic residues, persistent in the nature, are left,which display no toxicity towards warm-blooded animals, fish ormicroorganisms living in water.

Examples are given in the following paragraphs, which make clear the wayof preparation of the compounds claimed in the claim 1 of the generalformula I.

EXAMPLES Example 1 EthylN-{2-{4-[(cis-2-octadecanoyloxycyclohexyl)methyl]phenoxy}ethyl}carbamate (I)

Octadecanoyl chloride (1.06 mmol) was added to a solution of ethylN-{2-{4-[(cis-2-hydroxycyclohexyl)methyl]phenoxy}ethyl} carbamate (II;0.884 mmol) in benzene (10 ml) and in pyridine (0.4 ml), at 0° C. andunder stirring during 5 min. Then the cooling bath is removed and thereaction mixture is allowed to stir at 35° C. for 4 h. Then the reactionmixture is worked up by pouring onto a mixture of ice and hydrochloricacid (5:1, 30 ml), and organic layer is extracted with ether (3×30 ml).After drying over sodium sulfate and after removal of the solvent underreduced pressure, the residue is purified by column chromatography onsilica gel, affording 500 mg (96%) of the required product claimed inthe claim 1 of the general formula I. ¹H NMR (CDCl₃): 0.88 (t, J=6.8 Hz,3H), 1.23-1.93 (m, 39H), 1.25 (t, J=7.2 Hz, 3H), 2.35 (t, J=7.2 Hz, 2H),2.39 (dd, J=8.0 a 13.7 Hz, 1H), 2.55 (dd, J=6.8 a 13.7 Hz, 1H), 3.57(bq, J=5.4 Hz, 2H), 4.00 (t, J=5.1 Hz, 2H), 4.12 (q, J=7.2 Hz, 2H), 4.90(dt, J=2.6, 2.6 a 4.4 Hz, 1H), 5.11 (bt, J=5.4 Hz, 1H), 6.79 (m, 2H),7.00 (m, 2H). ¹³C NMR (CDCl₃): 14.11 (q), 14.60 (q), 20.85 (t), 25.27(t), 26.97 (t), 29.61 (t, 2C), 29.63 (t, 3C), 29.65 (t, 2C), 29.67 (t,2C), 29.69 (t, 6C), 31.92 (t), 34.86 (t), 37.76 (t), 40.50 (t), 42.56(d), 60.92 (t), 66.96 (t), 71.76 (d), 114.26 (d), 129.97 (d), 133.05(s), 156.66 (s), 156.73 (s), 173.36 (s). IR (CCl₄): 3464 (w), 3032 (w),1729 (s), 1612 (w), 1585 (w), 1510 (s), 1450 (m), 1243 (s), 1219 (s),1176 (s) cm⁻¹. FAB-MS (m/z) 588 (M⁺+1, 10), 560 (8), 520 (5), 483 (9),429 (10), 401 (11), 384 (13), 327 (15), 313 (98), 304 (35), 285 (30),267 (37), 215 (100), 214 (87), 187 (79). M.p.=78-80° C.

Example 2 EthylN-{2-{4-[(trans-2-octadecanoyloxycyclohexyl)methyl]phenoxy}ethyl}carbamate (I)

As described in the example 1, 485 mg (95%) of the compound claimed inthe claim 1 of the general formula I yielded starting from ethylN-{2-{4-[(trans-2-hydroxycyclohexyl)-methyl]phenoxy}ethyl} carbamate(II; 0.868 mmol) and octadecanoyl chloride (1.06 mmol) at 35° C., usingpyridine as base catalyst. ¹H NMR (CDCl₃): 0.88 (t, J=7.6 Hz, 3H),1.23-2.01 (m, 39H), 1.25 (t, J=7.1 Hz, 3H), 2.19 (dd, J=9.3 a 13.6 Hz,1H), 2.29 (t, J=7.6 Hz, 2H), 2.84 (dd, J=3.8 a 13.6 Hz, 1H), 3.57 (bq,J=5.2 Hz, 3H), 4.00 (t, J=5.1 Hz, 2H), 4.12 (q, J=7.1 Hz, 2H), 4.56 (dt,J=4.3, 10.1 a 10.1 Hz, 1H), 5.11 (bt, J=5.2 Hz, 1H), 6.80 (m, 2H), 7.02(m, 2H). ¹³C NMR (CDCl₃): 14.10 (q), 14.61 (q), 24.52 (t), 25.08 (t),29.60 (t, 2C), 29.63 (t, 2C), 29.65 (t, 2C), 29.66 (t, 3C), 29.69 (t,6C), 29.87 (t), 31.86 (t), 34.75 (t), 37.79 (t), 40.53 (t), 43.89 (d),60.93 (t), 67.00 (t), 76.47 (d), 114. 19 (d), 130.17 (d), 132.86 (s),156.63 (s), 156.71 (s), 173.59 (s). IR (CCl₄): 3464 (w), 3033 (w), 1729(s), 1612 (w), 1585 (w), 1509 (s), 1451 (m), 1243 (s), 1219 (s), 1176(s) cm⁻¹. FAB-MS (m/z) 588 (M⁺+1, 5), 503 (7), 459 (10), 429 (14), 415(10), 401 (6), 371 (11), 327 (10), 313 (23), 307 (21), 304 (25), 285(10), 257 (18), 232 (19), 215 (100), 214 (63), 187 (62). M.p.=64-65° C.

Example 3 EthylN-{2-{4-[(cis-2-(cis-9-octadecenoyl)oxycyclohexyl)methyl]phenoxy}ethyl}carbamate (I)

As described in the example 1, 207 mg (91%) of the compound claimed inthe claim 1 of the general formula I yielded starting from ethylN-{2-{4-[(cis-2-hydroxycyclohexyl)-methyl]phenoxy}ethyl} carbamate (II;0.389 mmol) and 9-cis-hexadecenoyl chloride (0.5 mmol) at 20° C., usingtriethylamine as base catalyst. ¹H NMR (CDCl₃): 0.88 (t, J=7.1 Hz, 3H),1.25-1.74 (mn, 19H), 1.85-1.95 (m, 1H), 1.98-2.05 (m, 2H), 2.36 (t,J=7.7 Hz, 2H), 2.39 (dd, J=7.9 a 13.6 Hz, 1H), 2.55 (dd, J=6.8 a 13.7Hz, 1H), 3.57 (bq, J=5.3 Hz, 2H), 4.00 (t, J=5.1Hz, 2H), 4.12 (q, J=7.1Hz, 2H), 4.91 (dt, J=2.7, 2.7 a 4.2 Hz, 1H), 5.12 (bt, J=5.4 Hz, 1H),5.31-5.38 (m, 2H), 6.79 (m, 2H), 7.00 (m, 2H). ¹³C NMR (CDCl₃): 14.08(q), 14.60 (q), 20.87 (t), 22.66 (t), 25.05 (t), 25.25 (t), 27.00 (t),27.17 (t), 27.22 (t), 29.14 (t), 29.21 (t), 29.23 (t), 29.31 (t), 29.51(t), 29.64 (t), 29.70 (t), 29.76 (t), 29.99 (t), 31.89 (t), 34.85 (t),37.75 (t), 40.53 (t), 42.56 (d), 60.92 (t), 66.99 (t), 71.80 (d), 114.30(d), 129.72 (d), 129.97 (d), 130.00 (d), 133.07 (s), 156.75 (s, 2C),173.31 (s). IR (CCl₄): 3464 (w), 3030 (w), 1729 (s), 1653 (w), 1612 (w),1585 (w), 1510 (s), 1449 (m), 1243 (s), 1220 (s), 1176 (s), 703 (w)cm⁻¹. FAB-MS (m/z) 586 (M⁺+1, 5), 391 (5), 304 (19), 176 (8), 149 (10),116 (100), 107 (44), 88 (70). Mp.=3940° C.

Example 4 EthylN-{2-{4-[(trans-2-(cis-9-octadecenoyl)oxycyclohexyl)methyl]phenoxy}ethyl}carbamate (I)

As described in the example 1, 209.5 mg (92%) of the compound claimed inthe claim 1 of the general formula I yielded starting from ethylN-{2-{4-[(cis-2-hydroxycyclohexyl)-methyl]phenoxy}ethyl} carbamate (II;0.389 mmol) and 9-cis-hexadecenoyl chloride (0.5 mmol) at 20° C., usingtriethylamine as base catalyst. ¹H NMR (CDCl₃): 0.90 (t, J=7.1 Hz, 3H),1.20-1.78 (m, 31H), 1.25 (t, J=7.1 Hz, 3H), 1.91-2.06 (m, 2H), 2.19 (dd,J=9.4 a 13.7 Hz, 1H), 2.35 (t, J=7.6 Hz, 2H), 2.84 (dd, J=3.6 a 13.7 Hz,1H), 3.57 (bq, J=5.4 Hz, 2H), 4.00 (t, J=5.1 Hz, 2H), 4.12 (q, J=7.1 Hz,2H), 4.57 (dt, J=4.3, 10.1 a 10.1 Hz, 1H), 5.10 (bt, J=5.3 Hz, 1H),5.30-5.41 (m, 2H), 6.80 (m, 2H), 7.02 (m, 2H). ¹³C NMR (CDCl₃): 14.09(q), 14.62 (q), 22.67 (t), 24.53 (t), 25.08 (t), 25.14 (t), 27.17 (t),27.22 (t), 29.18 (t), 29.31 (t), 29.32 (t), 29.52 (t), 29.60 (t), 29.70(t), 29.77 (t), 29.89 (t), 31.86 (t), 31.90 (t), 34.75 (t), 37.81 (t),40.56 (t), 43.90 (d), 60.94 (t), 67.04 (t), 76.48 (d), 114.23 (d),129.75 (d), 129.99 (d), 130.17 (d), 132.87 (s), 156.50 (s), 156.74 (s),173.53 (s). IR (CCl₄): 3464 (w), 3032 (w), 1728 (s), 1654 (w), 1612 (w),1585 (w), 1510 (s), 1451 (m), 1243 (s), 1221 (s), 1176 (s), 705 (w)cm⁻¹. FAB-MS (m/z) 586 (M⁺+1, 2), 558 (1), 514 (1), 391 (1), 304 (10),222 (3), 188 (2), 176 (4), 149 (9), 116 (100), 107 (15), 88 (39).M.p.=36-37° C.

Example 5 EthylN-{2-{4-[(cis-2-hexadecanoyloxycyclohexyl)methyl]phenoxy}ethyl}carbamate (I)

As described in the example 1, 225 mg (95%) of the compound claimed inthe claim 1 of the general formula I yielded starting from ethylN-{2-{4-[(cis-2-hydroxycyclohexyl)-methyl]phenoxy}ethyl} carbamate (II;0.424 mmol) and hexadecanoylchloride (0.509 mmol) at 70° C., usingquinoline as base catalyst. ¹H NMR (CDCl₃): 0.88 (t, J=7.1 Hz, 3H), 1.25(t, J=7.1 Hz, 3H), 1.25-1.74 (m, 34H), 1.90 (m, 1H), 2.36 (t, J=7.7 Hz,2H), 2.39 (dd, J=7.9 a 13.6 Hz, 1H), 2.55 (dd, J=6.8 a 13.6 Hz, 1H),3.57 (bq, J=5.3 Hz, 2H), 4.00 (t, J=5.0 Hz, 2H), 4.12 (q, J=7.1 Hz, 2H),4.90 (dt, J=2.6, 2.6 and 4.3 Hz, 1H), 5.10 (bt, J=5.4 Hz, 1H), 6.79 (m,2H), 7.00 (m, 2H). ¹³C NMR (CDCl₃): 14.10 (q), 14.62 (q), 22.68 (t),25.29 (t), 27.01 (t), 29.27 (t), 29.33 (t), 29.35 (t), 29.52 (t), 29.62(t, 2C), 29.65 (t, 2C), 29.68 (t, 2C), 29.69 (t, 2C), 30.00 (t), 31.92(t), 34.88 (t), 37.76 (t), 40.54 (t), 42.58 (d), 60.93 (t), 67.00 (t),71.79 (d), 114.32 (d), 129.98 (d), 133.10 (s), 156.76 (s, 2C), 173.33(s). IR (CCl₄): 3464 (w), 3032 (w), 1729 (s), 1612 (w), 1585 (w), 1510(s), 1449 (m), 1272 (m) cm⁻¹. FAB-MS (m/z) 560 (M⁺+1, 3), 476 (2), 415(1), 405 (2), 391 (3), 279 (19), 257 (5), 215 (9), 201 (30), 181 (16),165 (17), 149 (100), 110 (60). Mp.=78-80° C.

Example 6 EthylN-{2-{4-[(trans-2-hexadecanoyloxycyclohexyl)methyl]phenoxy}ethyl}carbamate (I)

As described in the example 1, 236 mg (99%) of the compound claimed inthe claim 1 of the general formula I yielded starting from ethylN-{2-{4-[(cis-2-hydroxycyclohexyl)-methyl]phenoxy}ethyl} carbamate (II;0.424 mmol) and hexadecanoylchloride (0.509 mmol) at 70° C., usingquinoline as base catalyst. ¹H NMR (CDCl₃): 0.88 (t, J=7.1H, 3H),0.89-1.74 (m, 35H), 1.25 (t, J=7.1 Hz, 3H), 2.19 (dd, J=9.3 a 13.6 Hz,1H), 2.29 (t, J=7.5 Hz, 2H), 2.84 (dd, J=3.7 a 13.6 Hz, 1H), 3.57 (bq,J=5.2 Hz, 2H), 4.00 (t, J=5.1 Hz, 2H), 4.12 (q, J=7.1 Hz, 2H), 4.56 (dt,3=4.4, 10.1 a 10.1 Hz, 1H), 5.10 (bt, 3=5.3 Hz, 1H), 6.80 (m, 2H), 7.03(m, 2H). ¹³C NMR (CDCl₃): 14.10 (q), 14.62 (q), 24.53 (t), 25.15 (t),29.20 (t), 29.28 (t), 29.35 (t, 2C), 29.48 (t, 2C), 29.65 (t, 2C), 29.68(t, 4C), 29.89 (t), 29.90 (t), 31.93 (t), 34.76 (t), 37.81 (t), 40.54(t), 43.90 (d), 60.92 (t), 67.03 (t), 76.47 (d), 114.22 (d), 130.18 (d),132.89 (s), 156.74 (s, 2C), 173.56 (s). IR (CCl₄): 3464 (w), 3033 (w),1728 (s), 1612 (w), 1585 (w), 1509 (s), 1451 (m), 1243 (s), 1219 (s),1176 (s) cm⁻¹. FAB-MS (m/z) 560 (M⁺+1, 8), 488 (3), 396 (1), 368 (1),340 (1), 303 (12), 262 (3), 115 (100), 88 (40), M.p.=67-68° C.

Example 7 EthylN-{2-{4-[(cis-2-butanoyloxycyclohexyl)methyl]phenoxy}ethyl} carbamate(I)

As described in the example 1, 142 mg (94%) of the compound claimed inthe claim 1 of the general formula I yielded starting from ethylN-{2-{4-[(cis-2-hydroxycyclohexyl)-methyl]phenoxy}ethyl} carbamate (II;0.384 mmol) and butanoyl chloride (0.418 mmol) at 20° C., using pyridineas base catalyst. ¹H NMR (CDCl₃): 1.00 (t, J=7.4 Hz, 3H), 1.20-1.51 (m,8H), 1.24 (t, J=7.2 Hz, 3H), 1.72 (m, 2H), 1.91 (m, 1H), 2.35 (t, J=7.5Hz, 2H), 2.39 (dd, J=8.2 a 13.6 Hz, 1H), 2.55 (dd, J=6.9 a 13.6 Hz, 1H),3.57 (bq, J=5.3 Hz, 2H), 4.00 (t, J=5.1 Hz, 2H), 4.12 (q, J=7.2 Hz, 2H),4.91 (dt, J=2.6, 2.6 a 4.4 Hz, 1H), 5.11 (bt, J=5.3 Hz, 1H), 6.79 (m,2H), 7.00 (m, 2H). ¹³C NMR (CDCl₃): 13.78 (q), 14.61 (q), 18.72 (t),20.86 (t), 25.05 (t), 26.99 (t), 29.99 (t), 36.78 (t), 37.74 (t), 40.52(t), 42.55 (d), 60.91 (t), 66.99 (t), 71.77 (d), 114.30 (d), 129.97 (d),133.06 (s), 156.64 (s), 156.74 (s), 173.13 (s). IR (CCl₄): 3464 (w),3033 (w), 1729 (s), 1612 (w), 1585 (w), 1510 (s), 1243 (s), 1176 (s),1095 (m) cm⁻¹. FAB-MS (m/z) 392 (M⁺+1, 35), 304 (21), 231 (8), 154 (9),137 (9), 116 (100), 107 (21), 88 (42), 71 (13). M.p.=82-84° C.

Example 8 EthylN-{2-{4-[(trans-2-butanoyloxycyclohexyl)methyl]phenoxy}ethyl} carbamate(I)

As described in the example 1, 113 mg (93%) of the compound claimed inthe claim 1 of the general formula I yielded starting from ethylN-{2-{4-[(cis-2-hydroxycyclohexyl)-methyl]phenoxy}ethyl} carbamate (II;0.384 mmol) and butanoyl chloride (0.418 mmol) at 20° C., using pyridineas base catalyst. ¹H NMR (CDCl₃): 0.96 (t, J=7.4 Hz, 3H), 1.24 (t, J=7.2Hz, 3H), 1.26-1.78 (m, 10H), 2.00 (m, 1H), 2.19 (dd, J=9.3 a 13.6 Hz,1H), 2.27 (t, J=7.5 Hz, 2H), 2.84 (dd, J=3.8 a 13.6 Hz, 1H), 3.57 (bq,J=5.3 Hz, 2H), 4.00 (t, J=5.1 Hz, 2H), 4.12 (q, J=7.2 Hz, 2H), 4.56 (dt,J=4.4, 10.1 a 10.1 Hz, 1H), 5.12 (bt, J=5.3 Hz, 1H), 6.80 (m, 2H), 7.03(m, 2H). ¹³C NMR (CDCl₃): 13.70 (q), 14.61 (q), 18.60 (t), 24.52 (t),25.09 (t), 29.91 (t), 31.87 (t), 36.64 (t), 37.84 (t), 40.56 (t), 43.89(d), 60.92 (t), 67.05 (t), 76.48 (d), 114.25 (d), 130.16 (d), 132.90(s), 156.66 (s), 156.75 (s), 173.35 (s). IR (CCl₄): 3464 (w), 3034 (w),1728 (s), 1612 (w), 1585 (w), 1509 (s), 1243 (s), 1177 (s), 1101 (m),1089 (m) cm⁻¹. FAB-MS (m/z) 392 (M⁺+1, 17), 320 (6), 304 (11), 222 (6),133 (6), 116 (100), 107 (37), 88 (45), 71 (13). M.p.=60-62° C.

Example 9

A Way of Screening of the Biological Activity of the Compound Claimed inthe claim 1 of the General Formula I Against Blowfly Neobellieria(Sarcophaga) bullata

A solution of the compound claimed in the claim 1 of the general formulaI in acetone (0.1%) was applied in a quantity of 5 microliters (5micrograms per female) to the upper part of thorax. Treated blowflyfemales were caged up together with intact (non-treated) males formating. The females were dissected in periodic intervals, and themorphological state of ovaries was checked—the egg shape, the degree ofyolk deposition in the first and in the second egg chamber, a level ofresorption of ovarioles and egg hatchability. The transformed (affected)ovaries were examined histologically.

Example 10

A Way of Screening of the Biological Activity of the Compound Claimed inthe claim 1 of the General Formula I Against Termite ProrhinotermesSimplex

Termites have only a sample of food treated with the compound claimed inthe claim 1 of the general formula I in the force feeding test (FF), buta choice between a sample of food treated with the compound claimed inthe claim 1 of the general formula I and a reference sample of foodtreated with acetone only. A treatment of the food samples with thecompound I claimed in the claim 1 has been made in at least twoconcentrations, 500 ppm and 5 ppm. A number of 60 pseudergates wasexposed to a treatment in each test, and each test is twice repeated.Each test has 16 days duration. The induction of the soldier castedifferentiation has been evaluated as the juvenilizing effect. Theresult is given in percents of the number of surviving individuals. Thejuvenoid methoprene has been used as the reference compound for testingof the biological activity of the compound I claimed in the claim 1. Theresults of screening of several structures corresponding the generalformula I claimed in the claim 1 in a concentration of 500 ppm are givenin Table 1.

TABLE 1 Juvenilizing effect of the tested structures of the generalformula I and that of methoprene in the concentrations of 500 ppm ontermite Prorrhinotermes simplex Compound (the reference compound or thecompound Juvenilizing of the general formula I) Method effect [%]Methoprene FF 1.3 Ethyl N-{2-{4-[(cis-2-octadecanoyloxycyclohexyl)- FF40.0 methyl]phenoxy}ethyl} carbamate (I) EthylN-{2-{4-[(trans-2-octadecanoyloxycyclohexyl)- FF 70.0methyl]phenoxy}ethyl} carbamate (I) EthylN-{2-{4-[(cis-2-(cis-9-octadecenoyl)oxycyclohexyl)- FF 93.7methyl]phenoxy}ethyl} carbamate (I) EthylN-{2-{4-[(trans-2-(cis-9-octadecenoyl)oxycyclohexyl)- FF 64.7methyl]phenoxy}ethyl} carbamate (I) EthylN-{2-{4-[(cis-2-hexadecanoyloxycyclohexyl)- FF 89.1methyl]phenoxy}ethyl} carbamate (I) EthylN-{2-{4-[(trans-2-hexadecanoyloxycyclohexyl)- FF 90.1methyl]phenoxy}ethyl} carbamate (I) EthylN-{2-{4-[(cis-2-butanoyloxycyclohexyl)- FF 86.1 methyl]phenoxy}ethyl}carbamate (I) Ethyl N-{2-{4-[(trans-2-butanoyloxycyclohexyl)- FF 87.4methyl]phenoxy}ethyl} carbamate (F)

Industrial Application

The compound I claimed in the claim 1 are applicable in the areas ofinsect population density control, especially in the area of socialhygiene, against cockroaches, termites and ants in the restaurant-typefacilities, hospitals, journal depositories, stories, houses etc. or inthe agricultural production, against moths, locusts, beetles, flies,mosquitoes etc.

What is claimed is:
 1. Esters derived from fatty acids and juvenoidalcohols of the general formula I,

in which X means the oxygen atom or the NH group, Y means the NH groupor the oxygen atom, R means methyl, ethyl, 1-propyl, 2-methylethyl orpropargyl and R′ means saturated or unsaturated alkyl with 4 to 22carbon atoms.
 2. A method of preparation of the compounds claimed in theclaim 1 of the general formula I based on a reaction of the juvenoidalcohol of the general formula II,

in which X means the oxygen atom or the NH group, Y means the NH groupor the oxygen atom and R means methyl, ethyl, 1-propyl, 2-methylethyl orpropargyl with a fatty acid chloride of the general formula III,R′COCl  (III) in which R′ means saturated or unsaturated alkyl with 4 to22 carbon atoms, under the continuous stirring, at 0 to 70° C., using aconvenient solvent, as toluene, xylene or benzene and under the presenceof a base catalyst, as triethylamine, pyridine or quinoline.
 3. Theapplication of the compounds claimed in the claim 1 of the generalformula I for the insect population density control, focused on controlof insects of the orders Isoptera, Blattodea, Diptera, Hymenoptera,Orthoptera, Coleoptera, and Lepidoptera.